1. Oldstyle (1783-1806)

Washington Irving was born in New York City on April 3, 1783, the eleventh (and eighth surviving) child of a moderately-successful merchant family. Born the month the American Revolution ended, Washington Irving was named for the war’s most famous general — and when that same general returned to the city six years later to be inaugurated as America’s first president, an aggressive nanny thrust the young Irving into George Washington’s face, demanding the president bless his namesake. Amused, Washington complied — an act of benevolence Washington Irving would remember (and embellish) all his life.

Irving was a poor student, more interested in pulp adventure novels than the classics, and completed his schooling with little math or science, and only a passable knowledge of grammar, punctuation and spelling. While Irving’s lack of academic progress disappointed his pious, business-minded Scotch father, his good nature had earned him the grudging respect of at least one teacher, who nicknamed Irving “The General” for his honesty. Throughout his teenage years, Irving remained far more interested in New York’s blooming social scene than academics, especially its rowdy and boisterous theater district.

At age eighteen, as a young man in search of a career, Irving landed in the law offices of prominent New York attorney Josiah Ogden Hoffman, where he struggled at law but found time to dabble at writing. He visited Canada on an extended business trip, during which he began his lifelong habit of keeping a journal (you can read an excerpt from Irving’s journal right here). In 1802, the nineteen-year-old Irving began writing letters to The Morning Chronicle, submitting droll commentaries on New York’s social and theater scene under the name of Jonathan Oldstyle — the first of many pseudonyms Irving would employ throughout his career. The letters caught the public’s fancy, giving Irving an early whiff of fame and moderate notoriety. They also proved to him that he could write — when he put his mind to it.

Concerned for his health — Irving often suffered coughing fits that raised eyebrows among his family — Irving’s brothers financed an extended tour of Europe for their youngest sibling. If the family hoped he would also acquire the cultivation needed to become a successful upper class merchant during his trip abroad, they were to be severely disappointed. While Irving bypassed most of the sites and locations considered essential for the development of an upwardly-mobile young man, he honed the social and conversational skills that would later make him one of the world’s most in-demand guests. He also suprised even himself by proving to be a remarkably adaptable traveler, noting in one letter that, “I endeavor to take things as they come with cheerfulness, and when I cannot get a dinner to suit my taste, I endeavor to get a taste to suit my dinner.” It was a credo that would guide him throughout his life, sometimes to the annoyance of his more easily-irritated detractors, who would snidely call him the “easily-pleased Washington Irving.”